| Full text | |
| Author(s): |
Piovan, Leandro
[1]
;
Kagohara, Edna
[1]
;
Ricci, Luis C.
[1]
;
Keppler, Artur F.
[1]
;
Capelari, Marina
[2]
;
Andrade, Leandro H.
[1]
;
Comasseto, Joao V.
[1]
;
Porto, Andre L. M.
[1, 3]
Total Authors: 8
|
| Affiliation: | [1] Univ Sao Paulo, Inst Quim, BR-05508900 Sao Paulo - Brazil
[2] Inst Bot, Secao Micol & Liquenol, BR-04301902 Sao Paulo - Brazil
[3] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Paulo - Brazil
Total Affiliations: 3
|
| Document type: | Journal article |
| Source: | TETRAHEDRON-ASYMMETRY; v. 19, n. 20, p. 2385-2389, OCT 20 2008. |
| Web of Science Citations: | 9 |
| Abstract | |
The use of whole cells of micro-organisms to bring about the biotransformation of an organic compound offers a number of advantages, but problems caused by enzymatic Promiscuity may be encountered upon With Substrates hearing more than one functional group. A one-pot screening method, in which whole fungal cells were incubated with a Mixture of 4-rnethylcyclohexanone I and phenyl methyl Sulfide 2, has been employed to determine the chemoselectivity of various biocatalysts. The hyphomycetes, Aspergillus terreus CCT 3320 and A. terreus URM 3571, catalysed the oxidation of 2 accompanied by the reduction of I to 4-methylcyclohexanol 1a and, for strain A. terreus CCT 3320, the Baeyer-Villiger oxidation of 1. The Basidomycetes, Trametes versicolor CCB 202, Pycnoporus sanguineus CCB 501 and Trichaptum byssogenum CCB 203, catalysed the oxidation of 2 and the reduction 1, but no Baeyer-Villiger reaction products were detected. In contrast. Trametes rigida CCB 285 catalysed the biotransformation of 1 to 1a, exclusively, in the absence of any detectable Sulfide oxidation reactions. The chemoselective reduction Of (+/-)-2-(phenylthio)cyclohexanone 3 by T. rigida CCB 285 afforded exclusively the (+)-cis-(1R,2S) and (+)-trans-(1S,2S) diastereoisomers of 2-(phenylthio)cyclohexan-1-ol 3a in moderate yields (13% and 27%, respectively) and high enantiomeric excesses (>98%). Chemoselective screening for the reduction of a ketone and/or the oxidation Of a Sulfide group in one pot by whole cells of micro-organisms represents an attractive technique with applications in the development of synthesis of complex molecule hearing different functional groups. (C) 2008 Published by Elsevier Ltd. (AU) | |